We recently connected with Cherilynn Castleman and have shared our conversation below.

Hi Cherilynn, thanks for joining us today. What’s the backstory behind how you came up with the idea for your business?

#1MillionWomenBy2030 Challenge Accepted –

A million women? Sounds like a lot, right? Well, I’ve always been a “dare” kind of gal when it comes to a game of truth or dare. And when someone dares me to do something, I don’t stop until it’s done. It turns out you’re never too old to play.

Jane Lovas, Ph.D., challenged me on her podcast to reach a million women by 2030. At first, I was worried. How will I reach a MILLION women in just 8 years? A MILLION? That’s two million ears and two million eyes. How could I possibly get that many people to see and hear me in less than a decade?

Well, while I’ve still got a long way to go, I’ve already come a long way – and I believe anyone can do the same!

I became a part of the #1MillionWomenBy2030 challenge because I want to see a million women of color sitting at the tables of their dreams by 2030. And by the tables of their dreams, I mean C-Suite, Sales Leadership, Sales Leaderboard, and Entrepreneurs’ tables.

Sounds easy enough (well, not really). But here’s the catch. These women are struggling to achieve their goals because most of them lack access to the tools, resources, and financial fluency they need to get there.

I want to coach and train a MILLION Black and Brown women by 2030. I want to train women who are too good to be ignored. I want to nurture women who, like me, are sick and tired of watching others take seats with THEIR names on ’em.

The secret, really, is that EVERYONE is a salesperson – whether you’re convincing your toddler to put their shoes on in the morning or telling the pale, stale, male authority figures in power that you should be at their table. As female leaders, we need to learn about products, we need to learn about money, and we need to learn about our OWN power when it comes to influencing people to buy into what you’re saying.

I’ve conquered my fair share of challenges in my life – and this one doesn’t scare me. I know what it’s like to feel like the only one in the room, but I also know what it takes to get the seat you deserve at the table you want. I WILL help a million women do the same by 2030. I hope you’ll be one of ‘em.

#1MillionWomenBy2030

Why 2023
For decades, the global workforce has marginalized black and brown women. Then, the pandemic came along, forcing many women to switch careers or quit the workforce entirely. Perhaps you’re one of them. But the good news is this – as the economy continues to recover, many of these Women of Color are rising with the resilience of the phoenix, building skills that can withstand anything—even the challenging headwinds on the horizon for 2023.

Think about it. No matter the state of the world, people will always need to buy something. And if you have the right sales training, you can sell a pink dress to a dedicated goth – or a CrossFit subscription to a couch potato.

I read an article about Ursula Burns, the former Xerox CEO, that inspired me. Ursula was interviewed in 2017 and highlighted the lack of black women in the C-Suite. She said, “HR isn’t going to get you there, ” and neither will Communications or the Arts. Ursula says that when it comes to a seat in the C-Suite, the “juice” lies with the people who are close to the product and, in turn, the money.

With the right sales training, women of color can sell themselves first as the best woman for the job, and once they’ve sunk their nails into the career of their dreams, the rewards won’t stop coming.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I have been in Sales since before girl scout cookies were 50 cents a box and have over 30 years of experience as a Fortune 500 Global Sales Executive. I want to see a million Women of Color (WoC) sit at the table of their dreams by 2030. But women must know how to sell to achieve this.

I believe every woman is one in a million. That’s why I give them the gentle nudge (well, shove) they need to take charge of their lives and make a change for the better – forever. But these women must know how to sell to the C-Suite to achieve this. They need to feel confident addressing a room full of men, commanding authority, and demanding respect using their God-given SUPERPOWERS. Whatever that may be. That’s why I coach and train women to be too good to be ignored.

I teach the key elements of successful sales, like deep relationships, immersing yourselves in the client’s world, leveraging empathetic listening and curiosity, and understanding how to use your superpowers to create customer solutions.

It’s easy to look at “great salespeople” and say, “they’re born with it.” But here’s the thing – selling is a skill, and like any other skill, it can be learned and mastered. Being able to sell ice to an Eskimo or Gucci to the CEO of Prada is a skill that will change your life. It’s a gateway talent that opens doors, breaks barriers, and gives you a VIP ticket to any table you want a seat at.

There’s no better time than now to get into sales and build a future you can be proud of.

I know firsthand what it takes to succeed as a sales professional. I know as an experienced entrepreneur the dedication, passion, and grit it takes to make your dreams a reality. As a single mom, I know the challenges of balancing family and a career and the stress of trying to do it all.

I’m also a LinkedIn Sales [In]sider and a Salesforce Tops Sales Influencer. Author: What’s in the C.A.R.D.S.?: 5 Post-Pandemic Sales Strategies

Let’s talk about resilience next – do you have a story you can share with us?

In 2009, I woke up in the intensive care unit from routine, minimally invasive spinal laminectomy surgery to excruciating pain and paralysis. Several months later, after two additional spinal surgeries, thirty days in intensive care, and months of rehab and physical therapy, I learned to walk with the assistance of a walker.

I arrived at my end-of-treatment appointment feeling proud of my accomplishment, but my neurosurgeon painted a miserable picture of my future. I was told I should expect additional surgeries in about a year. I should anticipate a life with chronic pain, medication, depression, disability, and, eventually, a wheelchair.

Refusing to accept his prognosis, I added a “Perfect Day” vision exercise to my morning routine. Every morning when I first woke up, I visualized my perfect day. I envisioned a detailed picture of my day, including the seven areas of my life (personal/social, work, family, spiritual, financial, intellect, and health/fitness). I included all five of my senses and imagined unlimited financial and technological resources in my picture.

I imagined what the flowers on my kitchen table smelled like while I stood watching my future husband make a healthy breakfast of yogurt and fresh fruit. I felt the warmth of the sun on my face as I cycled down a winding country road each morning. I experienced the delight of getting on a plane and flying to client and the joy walking into a meeting in a simple but elegant dress to speak with a team of professional women. And finally, I enjoyed the feel of crisp cotton sheets as I settled into bed after an active and busy day. (See the photo of how my vision became a reality).

In addition to my visioning exercise, I combined Western and Eastern medicine, utilizing acupuncture, herbal therapy, diet, meditation, physical exercise, and massage.

Fast forward to today. I never returned to my neurosurgeon, and I now live an active, almost pain-free life surrounded by family and friends. When I’m not traveling, coaching, or training, I bike, practice yoga, hike, golf, and kayak.

After a compelling value proposition, visioning is one of the most essential tools in a small business owner’s toolbox. A vision is a picture in your imagination that moves you. Executives and leaders have a vision. As a small business owner, your job is to help your clients paint a persuasive, passionate, and clear vision that motivates them to action. The good news is that this skill can be learned. And, like any skill, it can be developed over time with practice.

Today With kindness, self-love, and compassion, begin adding a “Perfect Day” exercise to your morning. Imagine your ideal day each morning before you get out of bed. Think big, really BIG. And, most important, when painting your picture, remember how amazing you truly are.

Can you tell us about what’s worked well for you in terms of growing your clientele?

Ask Powerful Questions

The 4 Fs – First, Finest, Failure, Future: The Discovery Interview

Conducting successful discovery interviews is critical. Frequently, prospects and even clients are ghosting small business owners. Asking powerful questions is the key to connecting and beginning the process of collaborative solutioning; and may reduce an inclination to ghost you.

Once you have done the usual client discovery and research, you’re financially fluent and have read your client’s website, executive bios, Form 10-K, annual reports, industry analyses, and press releases. What’s next? Let’s explore the holy grail to creating more excellent value and having more meaningful conversations with your customers to increase your pipeline and accelerate deals.

Here is a set of powerful questions that will strip away the noise and reveal customer insights to help you build better relationships, create client partnerships, and compel your clients into action.

When meeting with a new prospect, it is costly to downplay or miss an opportunity to make an authentic connection. One way to make this connection is to truly understand the client’s experience. It is one thing to have a prospective customer tell you about their pain; it is another if they tell you about their experience. You want to leverage your empathic listening skills to experience the situation as they truly experience it. Remember, that part of connecting is allowing yourself to be a little vulnerable or awkward with a new prospect or a current client.

Consider these powerful questions to help you connect with your customer and build better relationships, create client partnerships, and compel your clients into action.

During discovery calls, ask your clients, your client’s customers, or employees the First, Finest, Failure, and Future questions. The goal is to express genuine curiosity, not conduct an interrogation.

Here is an example of a “Discovery Call” with a Chief Technology Officer (CTO) – (Remember to “Make a statement, ask a question” so it’s a conversation and not an interrogation:

FIRST: Everyone has a “First” experience: First day on the job? First day launching a new technology? First day of the new quarter? First day with a new team?

Example: I remember the first time I realized I was responsible for driving strategy for my team; it was a little overwhelming. Do you remember the first time you thought about a strategy to manage disruption and drive technological change for your organization?

FINEST: We all have things we do well and are proud of.

Example: Many of my CTO clients tell me they are most proud when they gain a competitive edge or manage risk and uncertainty with technological innovation. Regarding scalable technology solutions, what do you and/or your team do well or are you most proud of?

FAILURE: We all have growth opportunities and wish to do something better. Always reposition “failure” as a positive. Ask, what could you do better or where you have a chance for growth?

Example: Many of my CTOs clients share that they wish their organization would train cross-functional teams to think like technologists; When it comes to scalable technology solutions, as a CTO, what do you wish you could do better?

FUTURE: Remember that growth begins with a vision and goals. Sales success comes from helping clients: 1) realize their vision; 2) develop and communicate their hopes, dreams, possibilities, and solutions; and 3) communicate their yardsticks – how they’re measured and the definition of success.

Example: When I think about the future, I want to champion the benefits of emerging technologies for my customers, vendors, and partners. If it was today’s date, in 2024, what would be your wish (goal, vision, dream, etc.) to drive organizational growth through technology?

Have fun and enjoy connecting with people, and business growth and success will follow.

Contact Info:

• Website: https://cherilynncastleman.com/
• Instagram: https://www.instagram.com/cherilynncastleman/
• Linkedin: https://www.linkedin.com/in/cherilynn-castleman/
• Twitter: https://twitter.com/masterfulgrowth
• Other: TikTok: https://www.tiktok.com/@cherilynncastleman?lang=en

Image Credits
I own these photos